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US20240360066A1 - Process for alkoxycarbonylation of olefins using synthesis gas - Google Patents

Process for alkoxycarbonylation of olefins using synthesis gas Download PDF

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US20240360066A1
US20240360066A1 US18/638,013 US202418638013A US2024360066A1 US 20240360066 A1 US20240360066 A1 US 20240360066A1 US 202418638013 A US202418638013 A US 202418638013A US 2024360066 A1 US2024360066 A1 US 2024360066A1
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Robert Franke
Matthias Beller
Peter KUCMIERCZYK
Ralf Jackstell
Yao Ge
Helfried Neumann
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Evonik Operations GmbH
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Evonik Oxeno GmbH and Co KG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
    • B01J2531/002—Materials
    • B01J2531/004—Ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium

Definitions

  • alkoxycarbonylation of ethylenically unsaturated compounds is a process of increasing significance.
  • An alkoxycarbonylation is understood to mean the reaction of ethylenically unsaturated compounds (olefins) with carbon monoxide and alcohols in the presence of a metal-ligand complex to give the corresponding esters.
  • the metal used is palladium.
  • the following scheme shows the general reaction equation for an alkoxycarbonylation:
  • the technical object of the invention is that of providing a novel process that delivers an increased yield.
  • the object is achieved by a process according to Claim 1 .
  • (C 1 -C 12 )-alkyl encompasses straight-chain and branched alkyl groups having 1 to 12 carbon atoms. These are preferably (C 1 -C 8 )-alkyl groups, more preferably (C 1 -C 6 )-alkyl, most preferably (C 1 -C 4 )-alkyl.
  • (C 3 -C 20 )-heteroaryl encompasses mono- or polycyclic aromatic hydrocarbon radicals having 3 to 20 carbon atoms, where one or more of the carbon atoms are replaced by heteroatoms. Preferred heteroatoms are N, O and S.
  • the (C 3 -C 20 )-heteroaryl groups have 3 to 20, preferably 6 to 14, particularly preferably 6 to 10 ring atoms.
  • pyridyl is in the context of this invention a C 6 -heteroaryl radical and furyl is a C 5 -heteroaryl radical.
  • CO is fed in with a pressure in the range from 1 MPa (10 bar) to 3 MPa (30 bar).
  • CO is fed in with a pressure in the range from 1.5 MPa (15 bar) to 2.5 MPa (25 bar).
  • CO is fed in with a pressure of 2 MPa (20 bar).
  • H 2 is fed in with a pressure in the range from 0.6 MPa (6 bar) to 2.9 MPa (29 bar).
  • H 2 is fed in with a pressure in the range from 0.9 MPa (9 bar) to 2.1 MPa (21 bar).
  • H 2 is fed in with a pressure in the range from 1 MPa (10 bar) to 2 MPa (20 bar).
  • the ratio of the pressures with which CO and H 2 are fed in is in the range from 1:0.3 to 1:1.4.
  • R 1 , R 3 are each selected from furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, furazanyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, benzofuranyl, indolyl, isoindolyl, benzimidazolyl, quinolyl, isoquinolyl.
  • R 2 and R 4 are ter Bu.
  • the ligand in process step b) has the formula (1):
  • the compound in process step c) comprising Pd is selected from palladium dichloride, palladium(II) acetylacetonate, palladium(II) acetate, dichloro(1,5-cyclooctadiene)palladium(II), bis(dibenzylideneacetone)palladium, bis(acetonitrile)dichloropalladium(II), (cinnamyl)palladium dichloride.
  • the compound in process step c) comprising Pd is Pd(acac) 2 .
  • the alcohol in process step d) is selected from methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, tert-butanol, 3-pentanol, cyclohexanol, phenol, or mixtures thereof.
  • the alcohol in process step d) is methanol.
  • the process comprises the additional process step d′) of: d′) adding an acid selected from: aluminium triflate, sulfuric acid, methylsulfonic acid (MSA), para-toluenesulfonic acid (p-TSA).
  • an acid selected from: aluminium triflate, sulfuric acid, methylsulfonic acid (MSA), para-toluenesulfonic acid (p-TSA).
  • aluminium triflate is added in process step d′).
  • the acid:ligand ratio is in the range from 1 mol:1 mol to 15 mol:1 mol.
  • the aluminium triflate:ligand ratio is in the range from 1 mol:1 mol to 15 mol:1 mol.
  • the reaction mixture is heated in process step f) of the process according to the invention preferably to a temperature in the range from 30° C. to 150° C., preferably from 40° C. to 140° C., more preferably from 50° C. to 120° C., in order to convert the olefin to an ester.
  • the invention is to be elucidated in detail hereinafter with reference to a working example.
  • the experiment was conducted once with synthesis gas and, as a comparative experiment, with pure CO.
  • the synthesis gas here was a mixture of CO and H 2 .
  • CO was fed in with a pressure of 20 bar.
  • H 2 was likewise fed in at 20 bar, which established a total pressure of 40 bar.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Process for alkoxycarbonylation of olefins using synthesis gas.

Description

  • The invention relates to a process for alkoxycarbonylation of olefins using synthesis gas (=mixture of CO and H2).
  • The alkoxycarbonylation of ethylenically unsaturated compounds is a process of increasing significance. An alkoxycarbonylation is understood to mean the reaction of ethylenically unsaturated compounds (olefins) with carbon monoxide and alcohols in the presence of a metal-ligand complex to give the corresponding esters. Typically, the metal used is palladium. The following scheme shows the general reaction equation for an alkoxycarbonylation:
  • Figure US20240360066A1-20241031-C00001
  • Conventionally, an alkoxycarbonylation process is operated using CO. One is described in EP 4 001 256 A1. The feeding of H2 has to date been deliberately avoided since it was assumed that this would promote side reactions, for example a hydroformylation, and hence the conversion to the desired target product would decline.
  • The technical object of the invention is that of providing a novel process that delivers an increased yield.
  • The object is achieved by a process according to Claim 1.
  • Process comprising the process steps of:
      • a) initially charging an olefin;
      • b) adding a ligand of formula (I):
  • Figure US20240360066A1-20241031-C00002
      • where
      • R1 and R3 are each a —(C3-C20)-heteroaryl radical,
      • R2 and R4 are each —(C1-C12)-alkyl;
      • c) adding a compound comprising Pd;
      • d) adding an alcohol;
      • e) feeding in CO and H2, where the pressure with which H2 is fed in is at least 0.6 MPa (6 bar);
      • f) heating the reaction mixture from steps a) to e), to convert the olefin to an ester.
  • The expression (C1-C12)-alkyl encompasses straight-chain and branched alkyl groups having 1 to 12 carbon atoms. These are preferably (C1-C8)-alkyl groups, more preferably (C1-C6)-alkyl, most preferably (C1-C4)-alkyl.
  • The expression (C3-C20)-heteroaryl encompasses mono- or polycyclic aromatic hydrocarbon radicals having 3 to 20 carbon atoms, where one or more of the carbon atoms are replaced by heteroatoms. Preferred heteroatoms are N, O and S. The (C3-C20)-heteroaryl groups have 3 to 20, preferably 6 to 14, particularly preferably 6 to 10 ring atoms. Thus, for example, pyridyl is in the context of this invention a C6-heteroaryl radical and furyl is a C5-heteroaryl radical.
  • In one variant of the process, CO is fed in with a pressure in the range from 1 MPa (10 bar) to 3 MPa (30 bar).
  • In one variant of the process, CO is fed in with a pressure in the range from 1.5 MPa (15 bar) to 2.5 MPa (25 bar).
  • In one variant of the process, CO is fed in with a pressure of 2 MPa (20 bar).
  • In one variant of the process, H2 is fed in with a pressure in the range from 0.6 MPa (6 bar) to 2.9 MPa (29 bar).
  • In one variant of the process, H2 is fed in with a pressure in the range from 0.9 MPa (9 bar) to 2.1 MPa (21 bar).
  • In one variant of the process, H2 is fed in with a pressure in the range from 1 MPa (10 bar) to 2 MPa (20 bar).
  • In one variant of the process, the ratio of the pressures with which CO and H2 are fed in is in the range from 1:0.3 to 1:1.4.
  • In one variant of the process, R1, R3 are each selected from furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, furazanyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, benzofuranyl, indolyl, isoindolyl, benzimidazolyl, quinolyl, isoquinolyl.
  • In one variant of the process, R2 and R4 are terBu.
  • In one variant of the process, the ligand in process step b) has the formula (1):
  • Figure US20240360066A1-20241031-C00003
  • In one variant of the process, the compound in process step c) comprising Pd is selected from palladium dichloride, palladium(II) acetylacetonate, palladium(II) acetate, dichloro(1,5-cyclooctadiene)palladium(II), bis(dibenzylideneacetone)palladium, bis(acetonitrile)dichloropalladium(II), (cinnamyl)palladium dichloride.
  • In one variant of the process, the compound in process step c) comprising Pd is Pd(acac)2.
  • In one variant of the process, the alcohol in process step d) is selected from methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, tert-butanol, 3-pentanol, cyclohexanol, phenol, or mixtures thereof.
  • In one variant of the process, the alcohol in process step d) is methanol.
  • In one variant of the process, the process comprises the additional process step d′) of: d′) adding an acid selected from: aluminium triflate, sulfuric acid, methylsulfonic acid (MSA), para-toluenesulfonic acid (p-TSA).
  • In one variant of the process, aluminium triflate is added in process step d′).
  • In one variant of the process, the acid:ligand ratio is in the range from 1 mol:1 mol to 15 mol:1 mol.
  • In one variant of the process, the aluminium triflate:ligand ratio is in the range from 1 mol:1 mol to 15 mol:1 mol.
  • The reaction mixture is heated in process step f) of the process according to the invention preferably to a temperature in the range from 30° C. to 150° C., preferably from 40° C. to 140° C., more preferably from 50° C. to 120° C., in order to convert the olefin to an ester.
  • The invention is to be elucidated in detail hereinafter with reference to a working example.
    • Experiment 1
  • Figure US20240360066A1-20241031-C00004
      • Pd (acac)2: 0.04 mol %
      • (1): 0.12 mol %
      • Al(OTf)3: 0.6 mol %
  • The experiment was conducted once with synthesis gas and, as a comparative experiment, with pure CO. The synthesis gas here was a mixture of CO and H2. In both experiments, CO was fed in with a pressure of 20 bar. In the experiment with synthesis gas, the H2 was likewise fed in at 20 bar, which established a total pressure of 40 bar.
  • Yield of ester:
      • CO: 47%
      • CO+H2:67%
    Experiment 2 (Variation of H2 Pressure)
  • Figure US20240360066A1-20241031-C00005
      • Pd (acac)2: 0.04 mol %
      • (1): 0.12 mol %
      • Al(OTf)3: 0.6 mol %
  • The series of experiments was conducted with a constant CO pressure of 20 bar. The H2 pressure was varied according to the table below.
  • p(H2) [bar] Yield [%]
    0 47
    5 44
    10 63
    20 67
    30 41
    40 41
  • As shown by the experiments conducted, the yield was increased by the use of synthesis gas.

Claims (15)

1. Process comprising the process steps of:
a) initially charging an olefin;
b) adding a ligand of formula (I):
Figure US20240360066A1-20241031-C00006
where
R1 and R3 are each a —(C3-C20)-heteroaryl radical,
R2 and R4 are each —(C1-C12)-alkyl;
c) adding a compound comprising Pd;
d) adding an alcohol;
e) feeding in CO and H2, where the pressure with which H2 is fed in is at least 0.6 MPa (6 bar);
f) heating the reaction mixture from steps a) to e), to convert the olefin to an ester.
2. Process according to claim 1,
wherein CO is fed in with a pressure in the range from 1 MPa (10 bar) to 3 MPa (30 bar).
3. Process according to claim 1,
wherein CO is fed in with a pressure in the range from 1.5 MPa (15 bar) to 2.5 MPa (25 bar).
4. Process according to claim 1,
wherein H2 is fed in with a pressure in the range from 0.6 MPa (6 bar) to 2.9 MPa (29 bar).
5. Process according to claim 1,
wherein H2 is fed in with a pressure in the range from 0.9 MPa (9 bar) to 2.1 MPa (21 bar).
6. Process according to claim 1,
wherein the ratio of the pressures with which CO and H2 are fed in is in the range from 1:0.3 to 1:1.4.
7. Process according to claim 1,
where R1, R3 are each selected from furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, furazanyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, benzofuranyl, indolyl, isoindolyl, benzimidazolyl, quinolyl, isoquinolyl.
8. Process according to claim 1,
where R2 and R4 are terBu.
9. Process according to claim 1,
wherein the ligand in process step b) has the formula (1):
Figure US20240360066A1-20241031-C00007
10. Process according to claim 1,
wherein the compound in process step c) comprising Pd is selected from palladium dichloride, palladium(II) acetylacetonate, palladium(II) acetate, dichloro(1,5-cyclooctadiene)palladium(II), bis(dibenzylideneacetone)palladium, bis(acetonitrile)dichloropalladium(II), (cinnamyl)palladium dichloride.
11. Process according to claim 1,
wherein the compound in process step c) comprising Pd is Pd(acac)2.
12. Process according to claim 1,
wherein the alcohol in process step d) is selected from methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, tert-butanol, 3-pentanol, cyclohexanol, phenol, or mixtures thereof.
13. Process according to claim 1,
wherein the alcohol in process step d) is methanol.
14. Process according to claim 1,
wherein the process comprises the additional process step d′) of:
d′) adding an acid selected from: aluminium triflate, sulfuric acid, methylsulfonic acid (MSA), para-toluenesulfonic acid (p-TSA).
15. Process according to claim 14,
wherein the acid:ligand ratio is in the range from 1 mol:1 mol to 15 mol:1 mol.
US18/638,013 2023-04-26 2024-04-17 Process for alkoxycarbonylation of olefins using synthesis gas Pending US20240360066A1 (en)

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